Vacation Rentals


Properties Available 41 properties available
Welcome to Casa Mariposa!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining seating 8, Living w/ TV on MAIN 2nd floor- Multiple screened in porches/lanai areas- 2 Twin XL Bedroom w/ TV, En-Suite Full Ba
Hot HOT 73
Casa Mariposa
Anna Maria
$480.00 - $1,800.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (7)
Welcome to Bateman's!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2543 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King
Hot HOT 59
Bateman's
Anna Maria
$560.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (11)
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience an extraordinary vacation at this stunning half-duplex on Anna Maria Island, ensuring an unparalleled escape.HIGHTLIGHTS:- Short Walk to the Beach- Open Kitche
Hot HOT 32
Island Girl East
Holmes Beach
$250.00 - $495.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Renovated, Designer Inspired, Ground Level Home on Beach Block Just Steps to Pristine Beaches of Anna Maria Island!HIGHLIGHTS:- Fully Equipped Kitchen, Dining, Living Room
Hot HOT 41
Anna Maria Aloha
Anna Maria Pet Friendly
$279.00 - $650.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
Welcome to Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Salty Pirate (#1678416), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Ple
Hot HOT 34
Seaswept Mermaid
Anna Maria
$400.00 - $1,400.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
Welcome to Coconut Lagoon!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Ground Level Completely Updated Luxury Historic Home3 Bed (sleeps 6), 2 1/2 Bath with Heated Pool easy walking distance to Pine Avenue and Gulf side beachesHIGHLIGHTS:- Kitchen, D
Hot HOT 62
Coconut Lagoon
Anna Maria Pet Friendly
$351.00 - $900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Welcome to Family Tides!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsThis listing is for the entire home including both units for a total of 6 bedrooms, 4 bathrooms, and private heated pool and rooftop deck for your personal and private use only.2288 sq. ft.HIGHLIGHTS:- 2 Separate Homes in One!- Each one level c
Hot HOT 23
Family Tides
Bradenton Beach
$600.00 - $1,600.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 5 (7)
Welcome to Sea Mist!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsElevated 3 Bed, 2 Bath in Anna Maria, Florida just STEPS to Pine Avenue & Anna Maria City PierSleeps 6, Max Occupancy 81742 Sq FtHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and ensuite full bath with walk in shower- 1
Hot HOT 49
Sea Mist
Anna Maria Pet Friendly
$360.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBeautifully updated, fresh, and clean elevated 3 Bed, 2.5 Bath which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue1500 square feetHIGHLIGHTS:-
Hot HOT 21
Sol Mate
Anna Maria Pet Friendly
$360.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (9)
Welcome to Sunset Margarita!Bradenton, Florida (Just OFF Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.Less than 2 miles from the Anna Maria Public Beach in the highly desirable brand new Margaritaville’s One Particular Harbour complex, clean, beautiful and bright!Thir
Hot HOT 14
Sunset Margarita
Off Island Pet Friendly
$225.00 - $432.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (1)
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2825 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower, Double Vanity, & Soaking Tub- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower- 1 Queen
Hot HOT 68
Sea La Vie Beach House
Anna Maria
$560.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
Welcome to Casa Posada!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Historic ground floor cottage but with all new interior paint and furnishings! Within easy walking distance to the gulf side beaches!DESCRIPTION:Casa Posada is a charming old Florida
Hot HOT 43
Casa Posada
Anna Maria Pet Friendly
$279.00 - $450.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (3)

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